diff --git a/src/index.cpp b/src/index.cpp
index 950f7e0b..cf09d922 100644
--- a/src/index.cpp
+++ b/src/index.cpp
@@ -3162,16 +3162,15 @@ void Index::search_field(const uint8_t & field_id,
         std::vector<token_t> truncated_tokens;
         num_tokens_dropped++;
 
-        size_t mid_index = (query_tokens.size() / 2);
-        if(num_tokens_dropped <= mid_index) {
+        if(num_tokens_dropped < query_tokens.size()) {
             // drop from right
-            size_t end_index = (query_tokens.size() - 1) - num_tokens_dropped;
+            size_t end_index = query_tokens.size() - num_tokens_dropped - 1;
             for(size_t i=0; i <= end_index; i++) {
                 truncated_tokens.emplace_back(query_tokens[i].position, query_tokens[i].value, query_tokens[i].prefix);
             }
         } else {
             // drop from left
-            size_t start_index = (num_tokens_dropped - mid_index);
+            size_t start_index = (num_tokens_dropped - query_tokens.size() + 1);
             for(size_t i=start_index; i<query_tokens.size(); i++) {
                 truncated_tokens.emplace_back(query_tokens[i].position, query_tokens[i].value, query_tokens[i].prefix);
             }
diff --git a/test/collection_grouping_test.cpp b/test/collection_grouping_test.cpp
index c5321b9e..3ea4fb3a 100644
--- a/test/collection_grouping_test.cpp
+++ b/test/collection_grouping_test.cpp
@@ -300,11 +300,12 @@ TEST_F(CollectionGroupingTest, GroupingWithMultiFieldRelevance) {
     ASSERT_STREQ("pop", results["grouped_hits"][0]["group_key"][0].get<std::string>().c_str());
     ASSERT_EQ(2, results["grouped_hits"][0]["hits"].size());
     ASSERT_STREQ("1", results["grouped_hits"][0]["hits"][0]["document"]["id"].get<std::string>().c_str());
-    ASSERT_STREQ("4", results["grouped_hits"][0]["hits"][1]["document"]["id"].get<std::string>().c_str());
+    ASSERT_STREQ("2", results["grouped_hits"][0]["hits"][1]["document"]["id"].get<std::string>().c_str());
 
     ASSERT_STREQ("rock", results["grouped_hits"][1]["group_key"][0].get<std::string>().c_str());
-    ASSERT_EQ(1, results["grouped_hits"][1]["hits"].size());
+    ASSERT_EQ(2, results["grouped_hits"][1]["hits"].size());
     ASSERT_STREQ("5", results["grouped_hits"][1]["hits"][0]["document"]["id"].get<std::string>().c_str());
+    ASSERT_STREQ("6", results["grouped_hits"][1]["hits"][1]["document"]["id"].get<std::string>().c_str());
 
     ASSERT_STREQ("country", results["grouped_hits"][2]["group_key"][0].get<std::string>().c_str());
     ASSERT_EQ(2, results["grouped_hits"][2]["hits"].size());
diff --git a/test/collection_specific_test.cpp b/test/collection_specific_test.cpp
index 0d1dc059..0d765bd3 100644
--- a/test/collection_specific_test.cpp
+++ b/test/collection_specific_test.cpp
@@ -2332,3 +2332,37 @@ TEST_F(CollectionSpecificTest, VerbatimMatchShouldNotOverpowerHigherWeightedFiel
     collectionManager.drop_collection("coll1");
 }
 
+TEST_F(CollectionSpecificTest, DropTokensTillOneToken) {
+    std::vector<field> fields = {field("title", field_types::STRING, false),
+                                 field("description", field_types::STRING, false),};
+
+    Collection* coll1 = collectionManager.create_collection("coll1", 1, fields).get();
+
+    nlohmann::json doc1;
+    doc1["id"] = "0";
+    doc1["title"] = "Harry";
+    doc1["description"] = "Malcolm Roscow";
+
+    nlohmann::json doc2;
+    doc2["id"] = "1";
+    doc2["title"] = "Malcolm";
+    doc2["description"] = "Something 2";
+
+    nlohmann::json doc3;
+    doc3["id"] = "2";
+    doc3["title"] = "Roscow";
+    doc3["description"] = "Something 3";
+
+    ASSERT_TRUE(coll1->add(doc1.dump()).ok());
+    ASSERT_TRUE(coll1->add(doc2.dump()).ok());
+    ASSERT_TRUE(coll1->add(doc3.dump()).ok());
+
+    auto results = coll1->search("harry malcolm roscow", {"title"},
+                                 "", {}, {}, {2}, 10, 1, FREQUENCY, {true}, 10).get();
+
+    ASSERT_EQ(1, results["hits"].size());
+    ASSERT_EQ("0", results["hits"][0]["document"]["id"].get<std::string>());
+
+    collectionManager.drop_collection("coll1");
+}
+